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Synthesis of steroids and related substances Communication 42. Condensation of 3,4,4a,7,8,8a-Hexahydro-4a-methyl-5-vinyl-2(1H)-naphthalenone with p-benzoquinone

โœ Scribed by I. N. Nazarov; G. P. Verkholetova; I. V. Torgov


Book ID
112436350
Publisher
Springer
Year
1959
Tongue
English
Weight
631 KB
Volume
8
Category
Article
ISSN
1573-9171

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โœ Akiko Saito; Akira Tanaka; Takayuki Oritani ๐Ÿ“‚ Article ๐Ÿ“… 1996 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 274 KB

An asymmetric synthesis of (-)-geosmin 1 via highly diastereoselective reduction of the enantiomerically pure title ketone 3 is described. Diisobutylaluminum hydride reduction of 3 in a mixed solvent of tetrahydrofuran and 1,2-dimethoxyethane led to aUylic alcohol 4 in 96% d.e., which by recrystalli